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It is eenerallv recomized that most routine chromato-
graphic techniq;es sh&ld he introduced to students within
the context of the undereraduate ornanic laboratorv. While a
substantial number of undergraduate organic experiments I
utilizing gas chromatography or thin-layer chromatography
have been published, there is a deficiency of those involving
high-performance liquid chromatography (HPLC). Herein
I IDMF DMF
smsnal. Mobile phase: msmanoi-waler (6040 ulv), 1.5 mumin. See ExpaC
mental Senion fw mlmn and other details.
Isomerization Procedure 'Roberts, R. M.; Gilbert. J. C.; Radewald, L. 6.; Wingove. A. S.;
Toa 10- X 15-mmtesttuhe wasadded 1.5 n L of dimethyl maleate Modem Experimental Organic Chemistry, 4th ed.; Saunders: New
(DMM) and six drops of 0.60 M bromine in carbon tetrachloride. York, 1985; p 168.
This operation should be carried out in a hood. The test tuhe was Kkasch, M. S.; Mansileld. J. V.; Mayo, F. R. J. Am. Chem. Soc.
corked and placed in direct sunlight (a south-facingwindow sill is lS37.59.1155. A more elaboratemechanism for this type of reaction
ideal for this purpose; alternatively a sun lamp may be used as an has been suasested. See Back. M. H.; Cvetanovic. R. J. Can. J. Chem
ultraviolet source) for 45 min. Crvstals of dimethvl fumarate (DMF) l963,4L 1566.
hegan to form almost immediatily. After the 45:min reaction pcri- A microspatual was used for this purpose. Only a small amount is
MI. s small amount of the crude pruduct wad removed7from t h lest
~ required-just enough to cover the tip of the spatula.